Learn to Lead

Bryan Clayton is the Co-Founder and CEO of GreenPal, an online marketplace that connects homeowners with local lawn care professionals. GreenPal has been called the “Uber for lawn care” by Entrepreneur magazine and has over 100,000 active users completing thousands of transactions per day. Before starting GreenPal, Bryan Clayton founded Peachtree Inc., one of the largest landscaping companies in the state of Tennessee, growing it to over $10 million a year in annual revenue before it was acquired by Lusa holdings in 2013. On this episode, we discussed Bryan’s journey into the tech world, what he’s learned about running a rapidly growing company, and being in it for the long haul. Bryan also shared some book recommendations and explained why as the CEO he still spends an hour or two doing direct customer support daily.

Erin Diehl is a veteran improviser from the top improvisational training programs in Chicago, including The Second City, i.O. Theater and The Annoyance Theatre. Erin conducts workshops across the country leveraging improvisational techniques to improve employees’ skills in corporate settings. Her work with clients such as United Airlines, PepsiCo, Deloitte, and The Obama Foundation earned her the 2014 Chicago RedEye Big Idea Award and has nominated her for the 2015-2019 Chicago Innovations Award. She is also a proud member of The Chicago Innovation Awards Women’s Cohort and a graduate of the Goldman Sachs 10,000 Small Business Program. On this episode, we discussed what improv has to do with the corporate world, how her first client set her on the path to make a leap into entrepreneurship, and her advice for anyone trying to manage their time wisely. FInally, we discussed why she is most proud in her career of successfully coercing over 12,000 professionals to chicken dance.

Wes Schroll is a serial entrepreneur who started his first company at 14-years old. After two small start up ventures, he wrote a business plan for what would one day become Fetch Rewards during his sophomore year at the University of Wisconsin-Madison. In March of 2021, Fetch closed its Series D round of financing with $220 Million led by SoftBank. Fetch is a bonafide "Unicorn" with a valuation of over $1 Billion. On this episode, we discuss some of the lessons Wes has learned along the way, how it felt for him to realize the Fetch Rewards app has more daily users than there are residents of New York City, and his trouble with productivity advice. Finally, Wes shares his approach to hiring leaders in his organization and why the two most important things he looks for are how well they understand the product and whether or not they can give and receive feedback. 

As we approach the new year, we wanted to share a short reflection on the time we've spent with you as listeners since we first launched the Learn to Lead Podcast only twenty-one months ago. Host Matt Confer encourages you to think a little about time passing using a short anecdote about great movies, time travel, and the moon landing (trust us!). We are incredibly grateful to get to share the airwaves with you and look forward to sharing new and exciting lessons from our guests in 2022.

Rita Gunther McGrath is a best-selling author, a sought-after speaker, and a longtime professor at Columbia Business School. She is widely recognized as a premier expert on leading innovation and growth during times of uncertainty. Rita has received the #1 achievement award for strategy from the prestigious Thinkers50 and has been consistently named one of the world’s Top 10 management thinkers in its bi-annual ranking. Rita is the author of the best-selling The End of Competitive Advantage. On this episode, we discussed her new book, Seeing Around Corners: How to Spot Inflection Points in Business Before They Happen, and its implications for learning leaders. Rita also shared her thoughts on the challenges and opportunities of innovation and what people often get wrong when thinking about it. Finally, Rita shared what makes her optimistic and what she's most curious about heading into the new year. 

Kim Kaupe is the founder of Bright Ideas Only where she has worked with Oprah, Paul McCartney, and Jimmy Buffett. Her first company, The Superfan Company, allowed her to work with everyone from Katie Perry to the Boston Red Sox. She was recognized as a Forbes 30 under 30, and by Inc Magazine, 35 under 35. She also received one of the highest offers on Season 5 of Shark Tank. On this episode, we discussed how she went from being an accidental entrepreneur to running a thriving marketing business, her best productivity tips, and how she prepares for a meeting. Finally, she shares how she’s dealt with imposter syndrome and how you can too.

Kara Goldin is the Founder and CEO of Hint, Inc., best known for its award-winning Hint® water, the leading unsweetened flavored water. She has been named one of InStyle’s Badass 50, Fast Company’s Most Creative People in Business, Fortune’s Most Powerful Women Entrepreneurs, Fortune's Most Innovative Women in Food & Drink and EY Entrepreneur of the Year for Northern California. Kara has successfully navigated the world of large companies and startups in many industries including media, tech and consumer products. On this episode, we discussed her motivations for founding Hint and the lessons she’s learned along the way. She shares how she comes up with ideas for new products and the benefits of not going in with all the answers figured out. Finally, she shares some tips for hiring well and leading a fast-growth company.